KR20080018857A - 기관 또는 조직에서 섬유증을 치료하기 위한 약제 제조용1-(치환된 페닐)-5-메틸-2-(1ｈ)-피리돈 - Google Patents
기관 또는 조직에서 섬유증을 치료하기 위한 약제 제조용1-(치환된 페닐)-5-메틸-2-(1ｈ)-피리돈 Download PDFInfo
- Publication number
- KR20080018857A KR20080018857A KR1020077018590A KR20077018590A KR20080018857A KR 20080018857 A KR20080018857 A KR 20080018857A KR 1020077018590 A KR1020077018590 A KR 1020077018590A KR 20077018590 A KR20077018590 A KR 20077018590A KR 20080018857 A KR20080018857 A KR 20080018857A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- pyridone
- fibrosis
- trifluoromethylphenyl
- akf
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000003814 drug Substances 0.000 title claims abstract description 34
- 206010016654 Fibrosis Diseases 0.000 title claims abstract description 24
- 230000004761 fibrosis Effects 0.000 title claims abstract description 24
- 210000000056 organ Anatomy 0.000 title claims abstract description 22
- -1 1- (substituted phenyl) -5-methyl-2- (1H) -pyridone Chemical class 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- JDZYVVUJIQYGRX-UHFFFAOYSA-N 1-(3-fluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(F)=C1 JDZYVVUJIQYGRX-UHFFFAOYSA-N 0.000 claims description 91
- 229940079593 drug Drugs 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 7
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 230000003176 fibrotic effect Effects 0.000 claims description 6
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 210000000626 ureter Anatomy 0.000 claims description 4
- IFCIIDXNZSQOPD-UHFFFAOYSA-N 1-(2,3-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Br)=C1Br IFCIIDXNZSQOPD-UHFFFAOYSA-N 0.000 claims description 2
- XYPVXRNOJDTEDJ-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Cl)=C1Cl XYPVXRNOJDTEDJ-UHFFFAOYSA-N 0.000 claims description 2
- MIUCEBJFPNOZFC-UHFFFAOYSA-N 1-(2,3-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(F)=C1F MIUCEBJFPNOZFC-UHFFFAOYSA-N 0.000 claims description 2
- BMLCFMLMGNOAPP-UHFFFAOYSA-N 1-(2,3-dimethoxyphenyl)-5-methylpyridin-2-one Chemical group COC1=CC=CC(N2C(C=CC(C)=C2)=O)=C1OC BMLCFMLMGNOAPP-UHFFFAOYSA-N 0.000 claims description 2
- JFBQYHYEBRHAPT-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=CC(C)=C1C JFBQYHYEBRHAPT-UHFFFAOYSA-N 0.000 claims description 2
- DIVMPFRJHNDQHW-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Cl)C=C1Cl DIVMPFRJHNDQHW-UHFFFAOYSA-N 0.000 claims description 2
- ICETYRMEWRWSJX-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(F)C=C1F ICETYRMEWRWSJX-UHFFFAOYSA-N 0.000 claims description 2
- XBUPCRKIBSIBGJ-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-5-methylpyridin-2-one Chemical group COC1=CC(OC)=CC=C1N1C(=O)C=CC(C)=C1 XBUPCRKIBSIBGJ-UHFFFAOYSA-N 0.000 claims description 2
- PQEYQPAPGLIVEI-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-5-methylpyridin-2-one Chemical group CC1=CC(C)=CC=C1N1C(=O)C=CC(C)=C1 PQEYQPAPGLIVEI-UHFFFAOYSA-N 0.000 claims description 2
- IXSFWFDBKAFHHA-UHFFFAOYSA-N 1-(2,5-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Br)=CC=C1Br IXSFWFDBKAFHHA-UHFFFAOYSA-N 0.000 claims description 2
- LUYVIZYIGZWLEK-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Cl)=CC=C1Cl LUYVIZYIGZWLEK-UHFFFAOYSA-N 0.000 claims description 2
- MDXCTWOGPDQWFR-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(F)=CC=C1F MDXCTWOGPDQWFR-UHFFFAOYSA-N 0.000 claims description 2
- IFJQAFSORYKHGW-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-5-methylpyridin-2-one Chemical group COC1=CC=C(OC)C(N2C(C=CC(C)=C2)=O)=C1 IFJQAFSORYKHGW-UHFFFAOYSA-N 0.000 claims description 2
- LVXOEVCZHWSZMZ-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-5-methylpyridin-2-one Chemical group CC1=CC=C(C)C(N2C(C=CC(C)=C2)=O)=C1 LVXOEVCZHWSZMZ-UHFFFAOYSA-N 0.000 claims description 2
- DMZNWOKZNPSKSP-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(Cl)C=CC=C1Cl DMZNWOKZNPSKSP-UHFFFAOYSA-N 0.000 claims description 2
- CXIJPJZPSZHTNT-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(F)C=CC=C1F CXIJPJZPSZHTNT-UHFFFAOYSA-N 0.000 claims description 2
- PIZBPTZVIPMEJT-UHFFFAOYSA-N 1-(2,6-dimethoxyphenyl)-5-methylpyridin-2-one Chemical group COC1=CC=CC(OC)=C1N1C(=O)C=CC(C)=C1 PIZBPTZVIPMEJT-UHFFFAOYSA-N 0.000 claims description 2
- BHBNMKITFOZDAB-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=C(C)C=CC=C1C BHBNMKITFOZDAB-UHFFFAOYSA-N 0.000 claims description 2
- QLFMOQVBGPZBAY-UHFFFAOYSA-N 1-(2-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1Br QLFMOQVBGPZBAY-UHFFFAOYSA-N 0.000 claims description 2
- LNCCSHHBXXNHHJ-UHFFFAOYSA-N 1-(2-fluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1F LNCCSHHBXXNHHJ-UHFFFAOYSA-N 0.000 claims description 2
- DCDSWTUVNHBRJZ-UHFFFAOYSA-N 1-(2-iodophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1I DCDSWTUVNHBRJZ-UHFFFAOYSA-N 0.000 claims description 2
- PPEKVFBDIFWVEV-UHFFFAOYSA-N 1-(3,4-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Br)C(Br)=C1 PPEKVFBDIFWVEV-UHFFFAOYSA-N 0.000 claims description 2
- GAHWJIZKEGFRLL-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-5-methylpyridin-2-one Chemical group C1=C(OC)C(OC)=CC=C1N1C(=O)C=CC(C)=C1 GAHWJIZKEGFRLL-UHFFFAOYSA-N 0.000 claims description 2
- KXSZGLHSEASUBA-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=C(C)C(C)=C1 KXSZGLHSEASUBA-UHFFFAOYSA-N 0.000 claims description 2
- RMHNSSKWHOINQA-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 RMHNSSKWHOINQA-UHFFFAOYSA-N 0.000 claims description 2
- CEKMQLXFPZYWRU-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-5-methylpyridin-2-one Chemical group COC1=CC(OC)=CC(N2C(C=CC(C)=C2)=O)=C1 CEKMQLXFPZYWRU-UHFFFAOYSA-N 0.000 claims description 2
- DLAIQUGBQRXOBE-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC(C)=CC(C)=C1 DLAIQUGBQRXOBE-UHFFFAOYSA-N 0.000 claims description 2
- MCAAQJLJBILPBZ-UHFFFAOYSA-N 1-(3-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Br)=C1 MCAAQJLJBILPBZ-UHFFFAOYSA-N 0.000 claims description 2
- QOXOVUCNQVZUEH-UHFFFAOYSA-N 1-(3-iodophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(I)=C1 QOXOVUCNQVZUEH-UHFFFAOYSA-N 0.000 claims description 2
- NUUFOILDYXVXLL-UHFFFAOYSA-N 1-(3-methoxyphenyl)-5-methylpyridin-2-one Chemical group COC1=CC=CC(N2C(C=CC(C)=C2)=O)=C1 NUUFOILDYXVXLL-UHFFFAOYSA-N 0.000 claims description 2
- PYZJZGLJFOVHRH-UHFFFAOYSA-N 1-(4-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Br)C=C1 PYZJZGLJFOVHRH-UHFFFAOYSA-N 0.000 claims description 2
- NNOLFDHGQTWVGS-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(F)C=C1 NNOLFDHGQTWVGS-UHFFFAOYSA-N 0.000 claims description 2
- HUSOSDHHWHLZRF-UHFFFAOYSA-N 1-(4-iodophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(I)C=C1 HUSOSDHHWHLZRF-UHFFFAOYSA-N 0.000 claims description 2
- CPJBLJUDFSFZEP-UHFFFAOYSA-N 1-[2,3-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=CC(C(F)(F)F)=C1C(F)(F)F CPJBLJUDFSFZEP-UHFFFAOYSA-N 0.000 claims description 2
- WMCCIACZTXJBNZ-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WMCCIACZTXJBNZ-UHFFFAOYSA-N 0.000 claims description 2
- NCNYJVDWMNCSPR-UHFFFAOYSA-N 1-[2,5-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC(C(F)(F)F)=CC=C1C(F)(F)F NCNYJVDWMNCSPR-UHFFFAOYSA-N 0.000 claims description 2
- QQOSQRFHCXTCMT-UHFFFAOYSA-N 1-[2,6-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=C(C(F)(F)F)C=CC=C1C(F)(F)F QQOSQRFHCXTCMT-UHFFFAOYSA-N 0.000 claims description 2
- JQCDQYWMVOPHJK-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JQCDQYWMVOPHJK-UHFFFAOYSA-N 0.000 claims description 2
- VYXSRCVSKXRDAN-UHFFFAOYSA-N 5-methyl-1-(2-methylphenyl)pyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=CC=C1C VYXSRCVSKXRDAN-UHFFFAOYSA-N 0.000 claims description 2
- NDGCMBKTLPWHDG-UHFFFAOYSA-N 5-methyl-1-(3-methylphenyl)pyridin-2-one Chemical group CC1=CC=CC(N2C(C=CC(C)=C2)=O)=C1 NDGCMBKTLPWHDG-UHFFFAOYSA-N 0.000 claims description 2
- RRHMWKBGPCGEOI-UHFFFAOYSA-N 5-methyl-1-[2-(trifluoromethyl)phenyl]pyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=CC=C1C(F)(F)F RRHMWKBGPCGEOI-UHFFFAOYSA-N 0.000 claims description 2
- IKTCWTVJVXLKRU-UHFFFAOYSA-N 5-methyl-1-[4-(trifluoromethyl)phenyl]pyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1 IKTCWTVJVXLKRU-UHFFFAOYSA-N 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 206010028594 Myocardial fibrosis Diseases 0.000 claims description 2
- 206010034665 Peritoneal fibrosis Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010050207 Skin fibrosis Diseases 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- BLHHEWJJZFVRNB-UHFFFAOYSA-N 1-(2,4-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Br)C=C1Br BLHHEWJJZFVRNB-UHFFFAOYSA-N 0.000 claims 1
- ZEICHSKCYQRIIG-UHFFFAOYSA-N 1-(2,6-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(Br)C=CC=C1Br ZEICHSKCYQRIIG-UHFFFAOYSA-N 0.000 claims 1
- NUFQXKSYNQFJSW-UHFFFAOYSA-N 1-(3,5-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(Br)=CC(Br)=C1 NUFQXKSYNQFJSW-UHFFFAOYSA-N 0.000 claims 1
- SGVKQHZMSAOGLV-UHFFFAOYSA-N 1-(3,5-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(F)=CC(F)=C1 SGVKQHZMSAOGLV-UHFFFAOYSA-N 0.000 claims 1
- LZWXKBBDHOJVPZ-UHFFFAOYSA-N 1-[3,4-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical group C1=C(C)C=CC(=O)N1C1=CC=C(C(F)(F)F)C(C(F)(F)F)=C1 LZWXKBBDHOJVPZ-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010060932 Postoperative adhesion Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 abstract description 57
- 229960003073 pirfenidone Drugs 0.000 abstract description 56
- 230000003510 anti-fibrotic effect Effects 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 30
- 241000700159 Rattus Species 0.000 description 27
- 210000001519 tissue Anatomy 0.000 description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 210000002966 serum Anatomy 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 239000002609 medium Substances 0.000 description 12
- 239000012679 serum free medium Substances 0.000 description 12
- 238000001356 surgical procedure Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 210000002950 fibroblast Anatomy 0.000 description 11
- 230000035755 proliferation Effects 0.000 description 10
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 9
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 9
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- 208000033679 diabetic kidney disease Diseases 0.000 description 9
- 210000002744 extracellular matrix Anatomy 0.000 description 9
- 241000699666 Mus <mouse, genus> Species 0.000 description 8
- 230000004663 cell proliferation Effects 0.000 description 8
- 230000003389 potentiating effect Effects 0.000 description 7
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 6
- 238000000134 MTT assay Methods 0.000 description 6
- 231100000002 MTT assay Toxicity 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000001028 anti-proliverative effect Effects 0.000 description 6
- 239000006143 cell culture medium Substances 0.000 description 6
- 230000001605 fetal effect Effects 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 5
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 5
- 210000003734 kidney Anatomy 0.000 description 5
- 210000004072 lung Anatomy 0.000 description 5
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 230000001575 pathological effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 4
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 description 3
- 108010006654 Bleomycin Proteins 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- 102000008070 Interferon-gamma Human genes 0.000 description 3
- 108010074328 Interferon-gamma Proteins 0.000 description 3
- 229960001561 bleomycin Drugs 0.000 description 3
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 3
- 229940044627 gamma-interferon Drugs 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000002107 myocardial effect Effects 0.000 description 3
- 210000003245 peritoneal mesothelial cell Anatomy 0.000 description 3
- 229960002957 praziquantel Drugs 0.000 description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 208000010159 IgA glomerulonephritis Diseases 0.000 description 2
- 206010021263 IgA nephropathy Diseases 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000003140 astrocytic effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229950010131 puromycin Drugs 0.000 description 2
- 238000011552 rat model Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 210000004872 soft tissue Anatomy 0.000 description 2
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- MJWRQZILSOKOTB-UHFFFAOYSA-N 1-(2-methoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC=CC=C1N1C(=O)C=CC(C)=C1 MJWRQZILSOKOTB-UHFFFAOYSA-N 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
- 108010061435 Enalapril Proteins 0.000 description 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000012449 Kunming mouse Methods 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 240000007182 Ochroma pyramidale Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 206010072170 Skin wound Diseases 0.000 description 1
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
- 208000031737 Tissue Adhesions Diseases 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 description 1
- 230000007131 anti Alzheimer effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
- 229960000873 enalapril Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 230000001037 epileptic effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 238000007490 hematoxylin and eosin (H&E) staining Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000000651 myofibroblast Anatomy 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 238000013059 nephrectomy Methods 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 210000004879 pulmonary tissue Anatomy 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000005084 renal tissue Anatomy 0.000 description 1
- 230000001084 renoprotective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008791 toxic response Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical group C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Gastroenterology & Hepatology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2005100314457A CN1846699A (zh) | 2005-04-13 | 2005-04-13 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
| CN200510031445.7 | 2005-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080018857A true KR20080018857A (ko) | 2008-02-28 |
Family
ID=37076581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077018590A Ceased KR20080018857A (ko) | 2005-04-13 | 2006-04-11 | 기관 또는 조직에서 섬유증을 치료하기 위한 약제 제조용1-(치환된 페닐)-5-메틸-2-(1ｈ)-피리돈 |
Country Status (10)
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10569792B2 (en) | 2006-03-20 | 2020-02-25 | General Electric Company | Vehicle control system and method |
| US10308265B2 (en) | 2006-03-20 | 2019-06-04 | Ge Global Sourcing Llc | Vehicle control system and method |
| US9733625B2 (en) | 2006-03-20 | 2017-08-15 | General Electric Company | Trip optimization system and method for a train |
| US8924049B2 (en) | 2003-01-06 | 2014-12-30 | General Electric Company | System and method for controlling movement of vehicles |
| WO2005047256A1 (en) | 2003-11-14 | 2005-05-26 | Shanghai Genomics, Inc. | The derivatives of pyridone and the use of them |
| CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
| ES2600460T3 (es) | 2005-05-10 | 2017-02-09 | Intermune, Inc. | Derivados de piridona-2-ona como moduladores del sistema de proteína cinasa activada por estrés |
| US8126601B2 (en) | 2006-03-20 | 2012-02-28 | General Electric Company | System and method for predicting a vehicle route using a route network database |
| US9689681B2 (en) | 2014-08-12 | 2017-06-27 | General Electric Company | System and method for vehicle operation |
| US8290645B2 (en) | 2006-03-20 | 2012-10-16 | General Electric Company | Method and computer software code for determining a mission plan for a powered system when a desired mission parameter appears unobtainable |
| US9156477B2 (en) | 2006-03-20 | 2015-10-13 | General Electric Company | Control system and method for remotely isolating powered units in a vehicle system |
| US8370006B2 (en) | 2006-03-20 | 2013-02-05 | General Electric Company | Method and apparatus for optimizing a train trip using signal information |
| CN101652138B (zh) * | 2007-09-19 | 2011-07-06 | 中南大学 | 1-取代芳基-2（1h）-吡啶酮化合物的新医药用途 |
| CN101235013A (zh) * | 2008-03-10 | 2008-08-06 | 广东东阳光药业有限公司 | 结晶型1-（3-氟苯基）-5-甲基-2-（1h）吡啶酮、其制备方法、及其组合物和应用 |
| CN102099036B (zh) | 2008-06-03 | 2015-05-27 | 英特芒尼公司 | 用于治疗炎性疾患和纤维化疾患的化合物和方法 |
| CN101918364B (zh) * | 2008-10-21 | 2013-02-13 | 史跃年 | 用于治疗高蛋白尿的药物组合物 |
| US7566729B1 (en) | 2008-11-10 | 2009-07-28 | Intermune, Inc. | Modifying pirfenidone treatment for patients with atypical liver function |
| US7635707B1 (en) | 2008-11-10 | 2009-12-22 | Intermune, Inc. | Pirfenidone treatment for patients with atypical liver function |
| US8016980B2 (en) | 2008-11-25 | 2011-09-13 | Dixie Consumer Products Llc | Paper products |
| US9834237B2 (en) | 2012-11-21 | 2017-12-05 | General Electric Company | Route examining system and method |
| CN101921225B (zh) * | 2009-06-11 | 2013-04-03 | 北京凯得尔森生物技术有限公司 | 吡啡尼酮类化合物、其制备方法和应用 |
| US7816383B1 (en) | 2009-12-04 | 2010-10-19 | Intermune, Inc. | Methods of administering pirfenidone therapy |
| US8084475B2 (en) * | 2009-12-04 | 2011-12-27 | Intermune, Inc. | Pirfenidone therapy and inducers of cytochrome P450 |
| US10105356B2 (en) | 2011-01-31 | 2018-10-23 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| CA2824432C (en) | 2011-01-31 | 2021-10-19 | Genoa Pharmaceuticals, Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| KR102057877B1 (ko) * | 2012-07-18 | 2019-12-20 | 노스 앤드 사우스 브라더 파마시 인베스트먼트 컴파니 리미티드 | 질소함유 헤테로고리 유도체 및 그의 약물에서의 용도 |
| CA2819967C (en) | 2012-08-31 | 2016-03-22 | Intermune, Inc. | Use of pirfenidone concomitantly with ciprofloxacin |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US9682716B2 (en) | 2012-11-21 | 2017-06-20 | General Electric Company | Route examining system and method |
| US9669851B2 (en) | 2012-11-21 | 2017-06-06 | General Electric Company | Route examination system and method |
| CN104725356B (zh) * | 2013-12-19 | 2017-02-22 | 广东东阳光药业有限公司 | 氮杂环衍生物及其在药物中的应用 |
| US9770443B2 (en) | 2014-01-10 | 2017-09-26 | Genoa Pharmaceuticals, Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| BR112016020987B1 (pt) | 2014-03-12 | 2023-11-14 | Western Sydney Local Health District | Método de identificação de receptores de aloenxerto renal e método de seleção de receptor do aloenxerto renal |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| CN113444783B (zh) | 2014-06-26 | 2024-04-09 | 西奈山伊坎医学院 | 通过分析预示性基因集诊断亚临床和临床的急性排异的方法 |
| WO2016044153A1 (en) * | 2014-09-18 | 2016-03-24 | Rush University Medical Center | Methods for preventing or treating osteoarthritis |
| DE102015217418A1 (de) | 2015-09-11 | 2017-03-16 | Mühlbauer Technology Gmbh | Radikalisch polymerisierbares Dentalmaterial |
| EP3308765B1 (de) | 2016-10-17 | 2022-07-13 | Mühlbauer Technology GmbH | Radikalisch polymerisierbare verbindung |
| WO2019011163A1 (en) * | 2017-07-14 | 2019-01-17 | Sunshine Lake Pharma Co., Ltd. | PROCESS FOR THE PREPARATION OF A PYRIMIDONE COMPOUND |
| US11572589B2 (en) | 2018-04-16 | 2023-02-07 | Icahn School Of Medicine At Mount Sinai | Method for prediction of acute rejection and renal allograft loss using pre-transplant transcriptomic signatures in recipient blood |
| CN113456636A (zh) * | 2021-07-09 | 2021-10-01 | 中南大学 | 一种氟非尼酮在制备急性肝损伤药物中的应用 |
| CN113274389B (zh) * | 2021-07-09 | 2022-11-08 | 中南大学 | 氟非尼酮在制备治疗急性肺损伤药物中的应用 |
| CN114716365B (zh) * | 2022-01-04 | 2024-03-01 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮化合物或其可药用盐在治疗肺纤维化中的应用 |
| WO2024235145A1 (zh) * | 2023-05-12 | 2024-11-21 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮及内过氧化物的制备和应用 |
| CN118526493A (zh) * | 2023-10-30 | 2024-08-23 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮化合物在治疗癌症和缓解纤维化中的应用 |
| CN120053452B (zh) * | 2023-11-30 | 2025-12-05 | 长沙晶易医药科技股份有限公司 | 一种2,4-二取代-5-氟嘧啶衍生物的新用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4042699A (en) | 1972-12-18 | 1977-08-16 | Affiliated Medical Research, Inc. | Method for reducing serum glucose levels |
| US3839346A (en) | 1972-12-18 | 1974-10-01 | Affiliated Med Res | N-substituted pyridone and general method for preparing pyridones |
| US4052509A (en) | 1972-12-18 | 1977-10-04 | Affiliated Medical Research, Inc. | Method for reducing serum uric acid levels |
| CA1049411A (en) | 1972-12-18 | 1979-02-27 | Affiliated Medical Research | N-substituted pyridone and general method for preparing pyridones |
| JPH02215719A (ja) * | 1989-02-15 | 1990-08-28 | Yamauchi Akitomo | 線維化病変組織の修復並びに線維化病変の阻止剤 |
| US5310562A (en) * | 1989-11-22 | 1994-05-10 | Margolin Solomon B | Composition and method for reparation and prevention of fibrotic lesions |
| US5518729A (en) | 1989-11-22 | 1996-05-21 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| US5716632A (en) * | 1989-11-22 | 1998-02-10 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| CN2114190U (zh) | 1992-01-09 | 1992-08-26 | 王刚 | 恒流一体化集成电源器件 |
| US5716623A (en) * | 1994-12-07 | 1998-02-10 | Immunex Corporation | Isolated Herpesvirus saimiri proteins that bind MHC Class II molecules |
| JP3496553B2 (ja) * | 1998-08-07 | 2004-02-16 | 株式会社高尾 | 弾球遊技機 |
| CN1218942C (zh) * | 2002-06-11 | 2005-09-14 | 中南大学湘雅医学院 | 抗纤维化吡啶酮化合物及其生产工艺方法 |
| CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
-
2005
- 2005-04-13 CN CNA2005100314457A patent/CN1846699A/zh active Pending
-
2006
- 2006-04-11 KR KR1020077018590A patent/KR20080018857A/ko not_active Ceased
- 2006-04-11 JP JP2008505716A patent/JP2008535871A/ja active Pending
- 2006-04-11 CN CN2006800002161A patent/CN1953749B/zh active Active
- 2006-04-11 WO PCT/CN2006/000651 patent/WO2006108354A1/zh not_active Ceased
- 2006-04-11 EP EP06722303A patent/EP1878428A4/en not_active Withdrawn
- 2006-04-11 RU RU2007141892/15A patent/RU2007141892A/ru not_active Application Discontinuation
- 2006-04-11 AU AU2006233433A patent/AU2006233433A1/en not_active Abandoned
- 2006-04-11 CA CA002603763A patent/CA2603763A1/en not_active Abandoned
- 2006-08-04 TW TW095128659A patent/TW200808315A/zh unknown
-
2007
- 2007-05-01 US US11/742,664 patent/US20090005424A9/en not_active Abandoned
-
2008
- 2008-09-04 US US12/204,629 patent/US20080319027A1/en not_active Abandoned
-
2009
- 2009-06-25 US US12/491,506 patent/US20090258911A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090005424A9 (en) | 2009-01-01 |
| RU2007141892A (ru) | 2009-05-20 |
| TW200808315A (en) | 2008-02-16 |
| US20070203203A1 (en) | 2007-08-30 |
| EP1878428A1 (en) | 2008-01-16 |
| CN1846699A (zh) | 2006-10-18 |
| WO2006108354A1 (fr) | 2006-10-19 |
| AU2006233433A1 (en) | 2006-10-19 |
| CN1953749A (zh) | 2007-04-25 |
| CN1953749B (zh) | 2010-04-14 |
| JP2008535871A (ja) | 2008-09-04 |
| CA2603763A1 (en) | 2006-10-19 |
| US20080319027A1 (en) | 2008-12-25 |
| US20090258911A1 (en) | 2009-10-15 |
| EP1878428A4 (en) | 2008-09-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20080018857A (ko) | 기관 또는 조직에서 섬유증을 치료하기 위한 약제 제조용1-(치환된 페닐)-5-메틸-2-(1ｈ)-피리돈 | |
| US9808461B2 (en) | Protection of renal tissues from ischemia through inhibition of the proliferative kinases CDK4 and CDK6 | |
| CN101406470A (zh) | 吡啶杂环衍生物的用途及含其的药物组合物 | |
| KR20130100381A (ko) | 피르페니돈 및 약학적으로 허용가능한 부형제의 캡슐 제제 | |
| JP2018048178A (ja) | オキサビシクロヘプタン類、および再灌流障害の治療のためのオキサビシクロヘプタン類 | |
| WO2016014342A2 (en) | Ang-(1-7) derviative oligopeptides and methods for using and producing the same | |
| KR20090005254A (ko) | 칼륨 채널 차단을 위한 약제학적 조성물 | |
| JP2002518449A (ja) | 高血中コレステロールを治療する組成物および方法 | |
| TW202313026A (zh) | 包含蛋白激酶抑制劑的藥物組合物及其醫藥用途 | |
| JP2008514636A (ja) | サイトカイン活性の低分子モジュレーター | |
| TWI885807B (zh) | 一類具有萘胺結構的小分子化合物的用途 | |
| CN115487191B (zh) | Quisinostat，一种新型的高效抗疟药物 | |
| JP2000309545A (ja) | 愛玩動物の年齢関連行動障害治療方法および治療用組成物 | |
| WO2017216579A1 (en) | Autophagy inducer compounds | |
| KR102676631B1 (ko) | 과민성 방광의 예방 또는 치료용 약학적 조성물 | |
| KR20070034070A (ko) | 신경병성 통증, 섬유근통 또는 류마티스성 관절염의 치료 | |
| CN115969975B (zh) | Phgdh抑制剂在预防和/或治疗结直肠癌转移中的应用 | |
| JPH07145129A (ja) | β−ナフトキノン誘導体及びそれらの塩類の新規な用途 | |
| WO2022106851A1 (en) | Mebendazole for use in the treatment of autosomal dominant polycystic kidney disease or autosomal recessive polycystic kidney disease | |
| JP2002540150A (ja) | ウイルス治療 | |
| JP2025532992A (ja) | エナボグリフロジンを含む心血管老化疾患の予防又は治療用薬学組成物｛ｐｈａｒｍａｃｅｕｔｉｃａｌ ｃｏｍｐｏｓｉｔｉｏｎ ｆｏｒ ｐｒｅｖｅｎｔｉｎｇ ｏｒ ｔｒｅａｔｉｎｇ ｃａｒｄｉｏｖａｓｃｕｌａｒ ａｇｉｎｇ ｄｉｓｅａｓｅｓ ｃｏｎｔａｉｎｉｎｇ ｅｎａｖｏｇｌｉｆｌｏｚｉｎ｝ | |
| CN120682118A (zh) | 一种化合物msb-2o及其制备方法和应用与预防或治疗弓形虫感染药物 | |
| Hawryluk et al. | Onchocerciasis drug discovery | |
| WO2024243490A2 (en) | Methods for addressing injection site reactions associated with the administration of bevemipretide | |
| CN120459090A (zh) | 化合物ctu-b2r在制备治疗弓形虫病的药物中的应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20070814 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20110411 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20130218 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20130930 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20130218 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |